2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside
• 英文别名: 2,3,4,6-tetra-O-benzyl-α-D-mannopyranose；2,3,4,6-tetra-O-benzyl-D-mannopyranose；2,3,4,6-Tetra-O-benzyl-alpha-D-mannopyranose；(2S,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ol
• 化学式: C₃₄H₃₆O₆
• 分子量: 540.656
• InChiKey: OGOMAWHSXRDAKZ-ZOHVZMGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 在 偶氮二异丁腈 、 氧气 、 铜 、 N,N-二异丙基乙胺 、 乙酰丙酮 、 锌 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 Phosphoric acid (2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester; compound with triethyl-amine
  参考文献：
  名称：

  An approach to the synthesis of aldosyl phosphates via aldosyl phosphites

  摘要：

  DOI：

  10.1016/0008-6215(82)85040-4
• 作为产物：
  描述：

  甲基-D-丙噻 在 硫酸 、 溶剂黄146 、 potassium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 29.5h， 生成 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Desmuramyl Dipeptides Modified by Adamantyl-1,2,3-triazole

  摘要：

  村苷二肽（MDP）是能够触发免疫应答的最小的肽聚糖片段。对MDP的结构修饰可以导致制备具有改良的免疫刺激性能的类似物，包括去杆二肽（DMPs）。本研究的目的是制备含有去杆二肽（L-Ala-D-Glu）的脂肪基三唑基团及其甘露糖衍生物，以研究它们在体内的免疫调节活性。通过在小鼠模型中使用卵清蛋白作为抗原，评估所制备化合物的佐剂活性，并与参考佐剂ManAdDMP进行比较。结果显示，在L-Ala-D-Glu的C-末端引入亲脂性脂肪基三唑基团有助于DMP的免疫刺激活性，并且将含有脂肪基三唑基团的DMP进行甘露糖化会增强其免疫刺激活性。

  DOI：

  10.3390/molecules26216352

文献信息

• Stereoselective Synthesis of 1,1′‐Disaccharides by Organoboron Catalysis
  作者：Sanae Izumi、Yusuke Kobayashi、Yoshiji Takemoto

  DOI：10.1002/anie.202004476

  日期：2020.8.10

  2‐dihydroxyglycosyl acceptors and glycosyl donors in the presence of a tricyclic borinic acid catalyst. In this reaction, the complexation of the diols and the catalyst is crucial for the activation of glycosyl donors, as well as for the 1,2‐cis‐configuration of the products. The anomeric stereochemistry of the glycosyl donor depends on the employed glycosyl donor. Applications of the produced 1,1′‐disaccharides are

  在三环硼酸催化剂存在下，通过使用1,2-二羟基糖基受体和糖基供体可以实现1,1'-二糖的高度立体选择性合成。在该反应中，二醇和催化剂的络合对于糖基供体的活化以及产物的1,2-顺式构型至关重要。糖基供体的异头立体化学取决于所用的糖基供体。还描述了产生的1,1'-二糖的应用。
• A new approach to construct full-length glycosylphosphatidylinositols of parasitic protozoa and [4-deoxy-Man-III]-GPI analogues
  作者：Asif Ali、D. Channe Gowda、Ram A. Vishwakarma

  DOI：10.1039/b414119a

  日期：——

  A new [2 + 2 + 2] approach to construct GPI molecules through the efficient synthesis of glucosamine-inositol and tetramannose intermediates led to a total synthesis of a GPI-anchor of Trypanosoma cruzi, and also afforded a key intermediate for the synthesis of valuable [4-deoxy-Man-III]-GPI analogues.

  通过高效合成葡糖胺-肌醇和四甘露糖中间体，一种新的[2+2+2]方法构建GPI分子，实现了Trypanosoma cruzi的GPI锚的完全合成，并提供了一种合成有价值[4-脱氧-甘露糖-III]-GPI类似物所需的关键中间体。
• Total synthesis of the fully lipidated glycosylphosphatidylinositol (GPI) anchor of malarial parasite Plasmodium falciparum
  作者：Asif Ali、Ram A. Vishwakarma

  DOI：10.1016/j.tet.2010.04.014

  日期：2010.6

  We report a new and convergent strategy for the total synthesis of fully lipidated glycosylphosphatidylinositol (GPI) anchor, the major pro-inflammatory factor of malarial parasite (Plasmodium falciparum). The key features of our approach include, the access to the key glucosamine–inositol intermediate by a novel route without a priori resolution of myo-inositol, convergent assembly of the tetramannose

  我们报告了完全脂化的糖基磷脂酰肌醇（GPI）锚，疟疾寄生虫（恶性疟原虫）的主要促炎因子的总合成的一种新的和会聚的策略。我们方法的关键特征包括：无需先验解决肌醇就可通过新颖途径获得关键的氨基葡萄糖-肌醇中间体，四甘露糖聚糖结构域的收敛组装，可将三种脂肪酸放置在所需脂肪酸中的灵活性最后步骤中的顺序，并有机会构建GPI类似物/模拟物，以探究疟原虫中GPI锚定途径的生物合成，免疫学和细胞生物学。
• Methods And Systems For Growing Plants Using Silicate-Based Substrates, Cultivation Of Enhanced Photosynthetic Productivity And Photosafening By Utilization Of Exogenous Glycopyranosides For Endogenous Glycopyranosyl-Protein Derivatives, And Formulations, Processes And Systems For The Same
  申请人：Innovation Hammer, LLC

  公开号：US20140331555A1

  公开（公告）日：2014-11-13

  Methods for promoting plant growth based on novel photosafening treatment regimes with glycopyranosides including glycopyranosylglycopyranosides, and aryl-a-D-glycopyranosides, and more specifically, with one or more compounds comprising terminal mannosyl-triose, optionally in the presence of light enhanced by one or more light reflecting and/or refracting members such as silicon-based substrates. Furthermore, chemical synthesis processes for the above compounds are disclosed for general application to plants. Silicate microbeads of the like are distributed over the ground or substrate in which roots of a plant are supported and planted, beneath and around a plant in a manner that light is refracted or reflected toward the phylloplane.

  基于新型光保护处理方案促进植物生长的方法，包括甘露聚糖苷类化合物，如甘露聚糖苷和芳基-a-D-甘露聚糖苷，更具体地，使用含有端基甘露三糖的一个或多个化合物，可选地在存在硅基基底等一个或多个反射和/或折射光的成员的情况下增强光线。此外，还公开了上述化合物的化学合成过程，以供普遍应用于植物。类似的硅酸盐微珠分布在植物的根部支撑和种植的地面或基质上，在植物的下方和周围，使光线以折射或反射的方式朝向叶面。
• Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity
  作者：Chun‐Wei Chang、Chia‐Hui Wu、Mei‐Huei Lin、Pin‐Hsuan Liao、Chun‐Chi Chang、Hsiao‐Han Chuang、Su‐Ching Lin、Sarah Lam、Ved Prakash Verma、Chao‐Ping Hsu、Cheng‐Chung Wang

  DOI：10.1002/anie.201906297

  日期：2019.11.18

  Stereocontrolled chemical glycosylation remains a major challenge despite vast efforts reported over many decades and so far still mainly relies on trial and error. Now it is shown that the relative reactivity value (RRV) of thioglycosides is an indicator for revealing stereoselectivities according to four types of acceptors. Mechanistic studies show that the reaction is dominated by two distinct intermediates:

  尽管数十年来进行了大量的努力，但立体控制的化学糖基化仍然是一个主要挑战，到目前为止，仍然主要依靠反复试验。现在表明，硫糖苷的相对反应性值（RRV）是根据四种受体揭示立体选择性的指标。机理研究表明，该反应由两种不同的中间体控制：糖基三氟甲磺酸酯和来自N-卤代琥珀酰亚胺（NXS）/ TfOH的糖基卤化物。糖基卤化物的形成与α-糖苷的产生高度相关。这些发现使得能够通过使用RRV作为α/β-选择性指示剂来预见糖基化反应，并且为立体控制糖基化开发了指导方针和规则。